1. Consider the reaction between 0.3 mL of acetic anhydride and 138 mg of salicy
ID: 1075965 • Letter: 1
Question
1. Consider the reaction between 0.3 mL of acetic anhydride and 138 mg of salicylic acid (see balanced reaction below) C3 C OH OH salicylic acid acetic anhydride aspirin acetic acid What mass (in grams) of acetic anhydride was added? What is the maximum amount of aspirin that can be produced from this amount of acetic anhydride? What is the maximum amount of aspirin capable of being produced from the starting 138 mg of salicylic acid? a. b. c. d. Which reagent is the limiting reagent? e. What is the theoretical yield of the reaction? f. Which compound would be expected to have a higher boiling point, salicylic acid of aspirin? Why?Explanation / Answer
density of acetic anhydride is 1.08 gm / ml.
a) mass of acetic anhydride added = density * volume = 1.08 * 0.3 = 0.324 gm.
0.324 gm acetic anhydride = mass / molar mass = 0.324 / 102.09 = 3.174 * 10^-3 mole.
138 mg = 0.138 gm salicylic acid = 0.138 / 138.121 = 9.99 * 10^-4 mole.
b) maximum amount of aspirin from acetic anhydride = 3.174 * 10^-3 * 108.157 = 0.572 gm = 572 mg
c) maximum amount of aspirin produced =9.99 * 10^-4 * 180.157 = 0.1799 gm = 179.9 mg = 180 mg.
e) theoretical yield of reaction = 9.99 * 10^-4 * 180.157 = 0.1799 gm = 179.9 mg = 180 mg.
theoretical yield of reaction is 180 mg.
d) salicylic acid is the limiting reactant.
f) salicylic acid contains polar -CO2H group but in aspirin this CO2H group is converted to ester group.
so effectiveness of hydrogen bonding is less in aspirin than salicylic acid.
so boiling point of aspirin is less than salicylic acid.
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